Synthesis of homo- and heteromultivalent carbohydrate-functionalized oligo(amidoamines) using novel glyco-building blocks
Synthesis of homo- and heteromultivalent carbohydrate-functionalized oligo(amidoamines) using novel glyco-building blocks
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DOI：
10.3762/bjoc.9.276
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发表时间：
2013-11-07
影响因子：
2.7
通讯作者：
Hartmann, Laura
中科院分区：
文献类型：
--
作者：
Wojcik, Felix;Lel, Sinaida;Hartmann, Laura
我们提出了固相合成的碳水化合物功能化的寡（酰胺胺）与不同的功能化模式，利用一种新的字母表的六个不同的糖基化的积木。硫代糖苷与二乙烯三胺前体的高效流动偶联是制备这些适用于全自动固相合成的结构单元的关键步骤。通过官能化结构单元而不是寡聚主链的后官能化引入糖配体允许直接合成多价糖配体，并完全控制单体序列和官能化模式。我们通过合成具有不同数量和间隔的碳水化合物的低聚物来展示这种构建块方法的潜力，并且还通过结合呈现不同单糖和二糖的构建块来展示异多价糖基化模式的可行性。
We present the solid phase synthesis of carbohydrate-functionalized oligo(amidoamines) with different functionalization patterns utilizing a novel alphabet of six differently glycosylated building blocks. Highly efficient in flow conjugation of thioglycosides to a double-bond presenting diethylentriamine precursor is the key step to prepare these building blocks suitable for fully automated solid-phase synthesis. Introduction of the sugar ligands via functionalized building blocks rather than postfunctionalization of the oligomeric backbone allows for the straightforward synthesis of multivalent glycoligands with full control over monomer sequence and functionalization pattern. We demonstrate the potential of this building-block approach by synthesizing oligomers with different numbers and spacing of carbohydrates and also show the feasibility of heteromultivalent glycosylation patterns by combining building blocks presenting different mono- and disaccharides.